1-(2-butoxy-6-hydroxyphenyl)ethanone | 63438-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-butoxy-6-hydroxyphenyl)ethanone
• CAS: 63438-68-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: UGINACRKJVEBIT-UHFFFAOYSA-N

物化性质

• 熔点：
  59–60°C
• 沸点：
  318.8±22.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-butoxy-6-hydroxyphenyl)ethanone 在 PPA 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 1-benzyl-4-n-butoxy-3-methyl-indazole
  参考文献：
  名称：

  在多磷酸（PPA）存在下，通过各种的环化反应合成取代的吲唑

  摘要：

  致力于发现一氧化氮合酶抑制剂的研究导致在多磷酸（PPA）存在下，通过取代的苯乙酮和二苯甲酮的各种azo的分子内环化反应，合成了一系列取代的吲唑。吲唑的结构通过元素分析，H nmr，ir和ms确定。

  DOI：

  10.1002/jhet.5570410420
• 作为产物：
  描述：

  正溴丁烷 、 2,6-二羟基苯乙酮 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-(2-butoxy-6-hydroxyphenyl)ethanone
  参考文献：
  名称：

  Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells

  摘要：

  To investigate the anti-proliferative effect of NF-kappa B inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NE-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-kappa B inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-kappa B inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NE-kappa B inhibition and anti-proliferative activity though the extent is not directly proportional to each other. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.045

文献信息

• NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
  申请人：SPHAERA PHARMA PVT. LTD.

  公开号：US20160039781A1

  公开（公告）日：2016-02-11

  The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.

  本发明提供了表儿茶素及相关多酚的新颖类似物，它们的各种官能化衍生物，以及它们的制备方法、包含这些化合物的组合物和它们的使用方法。
• One-Pot Access to 2-Aryl-3-(arylmethyl)chromones
  作者：Meng-Yang Chang、Kuan-Ting Chen、Yu-Lin Tsai、Han-Yu Chen

  DOI：10.1055/s-0039-1690760

  日期：2020.3

  o-hydroxyacetophenones with 2 equivalents of aryl­aldehydes provides 2-aryl-3-(arylmethyl)chromones (a chimera of flavone and homoisoflavanone) in MeOH at 50 °C under mild conditions. The uses of various bases and solvents are investigated for one-pot facile and efficient transformation. A plausible mechanism is proposed.

  邻位羟基苯乙酮与2当量芳基醛的氢氧化钠控制的分子间双羟醛缩合反应可在温和条件下于MeOH中于50°C的条件下提供2-芳基-3-（芳基甲基）色酮（黄酮和均异黄烷酮的嵌合体）。研究了各种碱和溶剂的使用，以实现一锅式便捷高效转化。提出了一个合理的机制。
• Synthesis and structure–activity relationships of novel IKK-β inhibitors. Part 3: Orally active anti-inflammatory agents
  作者：Toshiki Murata、Mitsuyuki Shimada、Sachiko Sakakibara、Takashi Yoshino、Tsutomu Masuda、Takuya Shintani、Hiroki Sato、Yuji Koriyama、Keiko Fukushima、Noriko Nunami、Megumi Yamauchi、Kinji Fuchikami、Hiroshi Komura、Akihiko Watanabe、Karl B Ziegelbauer、Kevin B Bacon、Timothy B Lowinger

  DOI：10.1016/j.bmcl.2004.05.041

  日期：2004.8

  A series of 2-amino-3-cyano-4-alkyl-6-(2-hydroxyphenyl)pyridine derivatives was synthesized and evaluated as IkappaB kinase beta (IKK-beta) inhibitors. Modification of a novel IKK-beta inhibitor 1 (IKK-beta IC50 = 1500 nM, Cell IC50 = 8000 nM) at the 4-phenyl ring and 6-phenol group on the pyridine core ring resulted in a marked increased in biological activities. An optimized compound, 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-piperidin-4-yl nicotinonitrile, exhibited excellent in vitro profiles (IKK-beta IC50 = 8.5 nM, Cell IC50 = 60 nM) and a strong oral efficacy in in vivo anti-inflammatory assays (significant effects at 1 mg/kg, po in arachidonic acid-induced ear edema model in mice). (C) 2004 Elsevier Ltd. All rights reserved.
• 2-SUBSTITUTED-5-HYDROXY-4H-CHROMEN-4-ONES AS NOVEL LIGANDS FOR THE SEROTONIN RECEPTOR 2B (5-HT2B)
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：US20170029399A1

  公开（公告）日：2017-02-02

  A family of compounds which function as selective ligands for the serotonin receptor 2B (5-HT 2B ) is identified. Some of the compounds are synthetic non-natural ligands which have a relatively strong interaction with 5-HT2B compared to naturally occurring compounds (some of which are identified for the first time herein as ligands for 5-HT 2B ). Because the compounds, both naturally occurring and synthetically produced, function as ligands for 5-HT 2B they will have application in, for example, the treatment and/or prevention of nervous system disorders such as Alzheimer's disease.
• Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells
  作者：Eeda Venkateswararao、Vinay K. Sharma、Jieun Yun、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2014.04.045

  日期：2014.7

  To investigate the anti-proliferative effect of NF-kappa B inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NE-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-kappa B inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-kappa B inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NE-kappa B inhibition and anti-proliferative activity though the extent is not directly proportional to each other. (C) 2014 Elsevier Ltd. All rights reserved.